Jesse Lipson is a self-taught software developer who became a full-time entrepreneur at age 23. In late 2005 he founded ShareFile, a file transfer service for businesses that need secure, reliable and easy data sharing tools. He launched ShareFile with $100 in Google AdWords spending and took the company from zero to four million users in six years. Citrix acquired ShareFile for $93 million in 2011 and today has more than 50,000 paying customers and several hundred employees. He held a variety of roles at Citrix over the next five years, including serving on the company’s executive leadership team as corporate vice president of cloud services.
Jesse also co-founded Raleigh Founded in 2012, a coworking community with over 400 member companies and 100,000 square feet under management.
Most recently, Jesse started a software company called Real Magic in late 2017. In 2018, Real Magic launched Levitate, a software product that helps small, relationship-based businesses stay in authentic, personal contact with customers, prospects and referral sources. .
He has a bachelor’s degree in philosophy from Duke University and is a member of the board of directors of Yext (NYSE: YEXT), Green Places, and Brooks Bell Inc., the company founded by his wife, Brooks Bell (who was also Discharge Question and answer theme Pete is… guest).
1. What’s in your pockets?
I always carry a handkerchief in my pocket, because I am a habitual sneezer and I always have the anxiety that if I sneeze I won’t have a handkerchief. So every morning I take a handkerchief and put it in my pocket.
Another thing I have in my pocket is a small four card case, because it’s much easier. It’s actually been a game changer, because not having to sit on a wallet all day and being able to slip this little thing into my pocket has been really nice. I keep a wallet and some cash in my backpack, but not carrying a wallet has been a nice productivity and convenience hack for me.
2. What exciting thing has recently happened to you or your organization?
Levitate is software designed for what we call relationship-based small businesses, and what we mean by relationship-based businesses are businesses that actually grow primarily through referrals and word of mouth. More of a “soft sell” process of staying in touch personally and authentically. We discovered that existing software, like MailChimp, is not personal. It is not authentic. Most people ignore those types of newsletters, or if they read them, it’s not the same as if someone contacted you with a personal email, text, or call. So what we’re trying to do is help relationship-based businesses scale that process of staying in touch personally and authentically, using some technology, content, and services.
As a company, we recently surpassed 3,500 paying customers, which has been very exciting. We launched a new industry vertical in nonprofits. So currently we’re focused on insurance, financial advisors, accounting firms, law firms, and now we’re starting to sell to non-profits as well.
The other exciting thing is that we have a new product that we’re launching, which I can’t talk too much about, but it’s coming out in early September. We’ve been working on it for the last year and it’s based on the Levitate platform, but it addresses a very different use case, a very different audience. So I’ve had a lot of fun working on the launch of this new product. [Note: Jesse talks a little more about the new product down below, including unveiling its name.]
3. What is your favorite coffee shop?
I am not a coffee drinker. I drink iced tea in the morning, so I don’t really go to coffee shops for the purpose of drinking coffee. My favorite breakfast place that I like to go to is Flying Biscuit. I have a stand up breakfast every Wednesday morning with a couple of my team at Flying Biscuit. So if you come to the Flying Biscuit on a Wednesday morning, you’ll probably see me there.
4. What keeps you up at night?
There is a lot to worry about right now. For the past six to nine months I have been following the macroeconomic picture more closely, which is not something a CEO of a small startup typically pays much attention to. But there are so many things to worry about and stay awake.
One concern is what is happening in the venture capital market. They are beginning to freeze due to the compression of valuations in public markets for high-growth technology companies. I’m also worried about inflation, the war in the Ukraine, the possible recession, that kind of thing.
5. What is your favorite restaurant or happy hour?
My go-to happy hour spot is Mordecai Brewery, because it’s right next to our office, so you’ll find me there. We often call it “Conference Room M” and sometimes we do one-on-one meetings there. At one point, they named a beer, “Levitate Beer,” after us and I think it was probably the best seller, so that’s my place there.
6. What’s next for you or your organization?
Levitate is truly evolving from a product to a powerful software platform. We are very excited to announce the launch of our new product, Coffee, built on the Levitate platform. We have also just announced an additional $6 million funding round to support our continued growth.
When I started this company, which was called Real Magic, the idea was that we were going to be a multi-product company. Surprisingly, in October it will be five years since I launched the company and that was the period of time when I decided it would be good to launch a second product. What is exciting for us is becoming a multi-product company.